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Nitrogen → 6-Phenyl-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897209
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인쇄 미리보기

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HRID 897209 반응식
N#N.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.C([O-])([O-])=O.[Cs+].[Cs+].[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>COCCOC.O.CCO>[C:37]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[O:10][C:9](=[O:14])[CH:8]=[C:7]3[NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:18][CH2:17]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
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참가 물질

6

반응물 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

생성물 1

HCID 737123446-Phenyl-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One수율 29.2%

시약·촉매·용매 1

HCID 86587095
Dimethoxyethane ethanol water
용매

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온도
160 °C

실험 절차

Into a dry microwave vial under N2 was added 6-bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(PPh3)Cl2 (about 1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). Phenyl boronic acid (5.6 mg, 0.046 mmol) was added and the solution was heated in the microwave for 5 minutes at 160° C., filtered, and was purified by Prep HPLC to give 5.86 mg (23%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 435 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.83-1.91 (m, 2H), 2.24 (br d, 2H), 3.15-3.23 (m, 2H), 3.61 (br d, 2H), 3.82-3.97 (m, 3H), 5.45 (s, 1H), 6.36-6.42 (m, 1H), 6.90 (d, 1H), 7.34-7.56 (m. 10H), 7.74 (d, 2H), 7.89 (dd, 1H), 8.40 (d, 1H).

후처리

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

출처 및 근거

ORD 기록
ord-81d4327024b24d73862f11ae421c328b
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06921821B2

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